Preparation, characterization and use of 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient, halogen-free and reusable ionic liquid catalyst for the trimethylsilyl protection of hydroxyl groups and deprotection of the obtained trimethylsilan

Novel 1,3-disulfonic acid imidazolium hydrogen sulfate, a halogen-free ionic liquid, is a recyclable and eco-benign catalyst for the trimethylsilyl protection of hydroxyl groups at room temperature under solvent free conditions to afford trimethylsilanes in excellent yields (92–100%) and in very short reaction times (1–5 min). Deprotection of the resulting trimethylsilanes can also be achieved using the same catalyst in methanol. The catalyst was characterized by IR, 1H NMR, 13C NMR and MS studies. All the products were extensively characterized by IR, 1H NMR, MS, and elemental and melting point analyses. This new method consistently has the advantages of excellent yields and short reaction times. Further, the catalyst can be recovered and reused for several times without loss of activity. The work-up of the reaction consists of a simple separation, followed by concentration of the crude product and purification.

Graphical abstractFigure optionsDownload full-size imageDownload high-quality image (89 K)Download as PowerPoint slideHighlights► Introduction of a new catalyst (as a halogen-free ionic liquid) for organic transformations. ► Introduction of an efficient method for the protection of alcohols and phenols. ► Generality of the method, high yields and short reaction times. ► Recoverability and reusability of the catalyst. ► Chemoselectivity and solvent-free nature of the reaction conditions.